Abstract
Complexation studies between two artificial receptors (molecular clefts of Rebek) naphthalene imide 5 and 5-azacytosine-β-naphthylethyl ester 9 and the antiviral nucleoside analog acyclovir 10 were performed and evaluated by determination of the equilibrium constants of 1:1 complexes using 1H and 13C NMR titrations as well as solubility titrations with reversed phase HPLC. The results showed an association between 9 and 10 but not between 5 and 10 through hydrogen bonding and π-stacking interactions and pointed out a complementarity between acyclovir 10 and the molecular cleft 9 similar to that observed with DNA guanine-cytosine base pairing. Docking simulations provide structural models of such interactions. The results so far obtained prompt us to propose 9 as a potential carrier for acyclovir 10.
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